Stumbling Blocks: How Great Leaders Are Made – Details, episodes & analysis

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Stumbling Blocks: How Great Leaders Are Made

Jonathan Block

Business

Frequency: 1 episode/13d. Total Eps: 27

Here, leaders share the moments along the way that have shaped them most deeply. Their stumbling blocks.

You'll hear leaders as they really are: challenged, battered, and deeply flawed. And you'll see them picking back up, dusting themselves off, and leading again. Because if we let them, stumbling blocks make us better.

Welcome to Stumbling Blocks: How Great Leaders are Made.

I’m your host, Jonathan Block. I've spent the last 20 years studying leadership, and I ask leaders to take us back to the moments that aren't on highlight reel:

• The day they got laid off.

• The crisis that almost broke them.

• The loss that re-shaped how they see the world.

Join me to uncover the stumbles that make leaders great.

Welcome to The Stumble.

Subscribe today.

Questions? Comments?
Linkedin: www.linkedin.com/in/jonathanfblock
Insta: @JonathanFBlock
Twitter: @JonathanFBlock
Email: Jonathan@BlockLeadershipGroup.com

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https://filotimofoundation.org/lung-run-2025/
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https://www.permanentequity.com/
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https://www.amazon.com/Turnaround-Time-Uniting-Employees-Friendly/dp/0063284286
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Sandra Sobieraj Westfall, fmr PEOPLE Mag DC Bureau Chief: The Price Of Saying "No"

Season 2 · Episode 3

Tuesday, October 13, 2026 • Duration 43:14

In 2016, a former PEOPLE reporter named Natasha Stoynoff said Donald Trump attacked her during an interview at Mar-a-Lago. Sandra Sobieraj Westfall, the Washington Bureau Chief for PEOPLE Magazine, made a business and editorial decision: She would stand by her friend and colleague. The magazine would cover the President's policies, but it would not cover his family the way it had covered every other First Family.

This is the story of that decision... and what happened next.

Sandra Sobieraj Westfall spent six years as a White House correspondent for the Associated Press and 20 years at PEOPLE. She went to 24 White House Correspondents' Dinners, flew on Air Force One, and interviewed First Families from both parties.

In the first of several conversations, we talk about the night a gunman tried to get into the Washington Hilton, and what Elizabeth Edwards taught her about grief.

Content note: This episode quotes President Trump's Access Hollywood remarks about women and discusses sexual assault and may not be suitable for children. President Trump has denied Natasha Stoynoff's account.

In this episode:

Where Sandra drew the line.
Ivanka Trump and "no hard feelings"
The morning the "bottom dropped out"
Starting over after 20 years: helping people in crisis tell their own stories

This episode is for leaders facing a values decision with risks associated, and for anyone who has been laid off and wondered what comes next.

Top 3 things I learned:

Being right doesn't protect your job.
You can lose a job without losing your dignity.
You get to decide what happens next.

Best experienced on YouTube, because Sandra shares hundreds of behind-the-scenes photos: http://www.youtube.com/@StumblingBlocksPodcast

Resources mentioned:

PEOPLE, "Physically Attacked by Donald Trump: A PEOPLE Writer's Own Harrowing Story" (Oct. 12, 2016)
Hillary Rodham Clinton, Something Lost, Something Gained: https://amzn.to/3TP0Ogd
Sandra's company, Storied Communication
Chapters: 0:00:00 Cold open: "We're Team Natasha"
0:00:31 Introduction
0:03:27 24 White House Correspondents' Dinners
0:06:11 Frank, the Secret Service and the freezer
0:08:02 The PEOPLE table and Rosario Dawson
0:10:04 The worst flacks
0:12:36 Her stumble: leaving the AP
0:16:32 The decision about Trump
0:17:04 Natasha Stoynoff's story
0:18:58 Donald Trump's own words
0:20:41 Would she do it differently?
0:22:51 PEOPLE stops covering politics
0:24:23 "No hard feelings"
0:26:41 Laid off
0:29:59 Starting over
0:30:44 Helping people in crisis tell their stories
0:33:30 What matters now

#Leadership #Decisions #Tradeoffs

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Tim Creasey, Chief Innovation Officer, Prosci: How To Lead Change

Season 2 · Episode 2

Friday, October 2, 2026 • Duration 37:53

Tim Creasey: Chief Innovation Officer, Prosci: How to Lead Change

Why do smart, well-run companies keep leading big changes that fail? Tim Creasey has spent 25 years at Prosci studying change management and shares the answer on this podcast.

Tim is Chief Innovation Officer at Prosci, the research firm behind the ADKAR Model, one of the most widely used change management frameworks in the world. We talk about why change is so hard for humans, why employees resist even the changes they asked for, and what leaders have to do differently to get people to adopt AI.

Tim also walks through the ABCs of sponsorship. Since Prosci's very first study, active and visible sponsorship has been the top contributor to change success, and Tim says it often separates the projects that succeed from the ones that fail by a three-to-one or four-to-one margin. He explains why executives can't delegate AI adoption, why AI is a new operating system rather than another tool, and why you should repeat your core message five to seven times without apologizing for it.

In this episode:

The ADKAR Model in plain English: Awareness, Desire, Knowledge, Ability, Reinforcement
Why AI adoption is different: it showed up in our pockets before it showed up at work
"That's the way we've always done it" and how to lead an exhausted workforce
Humans in the loop, humans leading the loop, and humans drawing the loops

For CEOs, CHROs, transformation leaders, HR leaders, and change practitioners leading digital transformation or an AI rollout.

Top things I learned:

Awareness means sharing why, not what. Telling people a change is coming is not the same as helping them understand why it matters.
Executives have to use AI themselves in order for their people to follow suit. You can't lead what you haven't touched.
Employees want two messengers. They want the business reasons for change from the top and the "what does this mean for me" from their direct supervisor.

Resources mentioned:

Scott Stanzel, Chief Communications Officer, Truist: 9/11 at the White House

Season 2 · Episode 2

Friday, September 11, 2026 • Duration 01:24:07

On 9/11/2001, Scott Stanzel was 28 years old, working his dream job at the White House when Secret Service agents came running down the halls, throwing open doors and shouting at everyone to get out. They had two minutes.

For twenty-five years, Scott has said almost nothing publicly about September 11th. "Over the years I've struggled with how to talk about my experiences or even acknowledge that day," he wrote once.

This is the first time he has sat for an interview to tell the whole story:

Time Chapter

02:36 9:37 a.m. and the phone call about the Pentagon

04:30 Smoke rising over the Old Executive Office Building

08:59 "There's another plane. You have two minutes."

09:53 "Take off your shoes and run"

11:08 The West Exec gates thrown open

11:58 How a 28-year-old landed a White House job

13:18 The crystal clear blue morning

15:30 Calling mom, who was out running errands

17:33 The cell network fails, and Washington switches to BlackBerrys

18:53 Anita and Tim McBride clear a floor for the White House

19:43 10:03 a.m., Shanksville, and the plane that was coming for them

22:11 What the passengers on United 93 pieced together

26:46 What the day was supposed to be: No Child Left Behind

29:20 8:46 a.m., the first plane, and "did the pilot have a heart attack?"

32:16 From national tragedy to act of war

33:27 The car bomb that never happened

37:03 President Bush at Barksdale Air Force Base

Jim Olson, Chief Communications Officer: How to Turn your Setback Story into your Comeback Legacy

Thursday, July 30, 2026 • Duration 48:47

Most crisis experts have never actually sat in the room when everything fell apart. Jim Olson has. He was head of communications at US Airways when Flight 1549 landed on the Hudson. He was at Starbucks when its flagship store in Jakarta was bombed. And he was at United Airlines the night Dr. David Dao was dragged off a plane and it became one of the first viral crises in business history.

Then the crisis came for him. In 2024 Jim was diagnosed with stage 4 melanoma that had spread to his lung and his brain. During treatment he lost his eyesight. He is now legally blind. And he wrote a book about all of it called Tailwind.

We talk about the 2am back pain that had no medical explanation and ended up saving his life. The "do hard things" tattoo he got a month before he went blind. And why he now prays in gratitude for the healing that's already happening instead of begging for the healing he wants.

If you're carrying something heavy right now, this one is for you.

In this episode:

00:00 The monster storm none of us escapes
00:25 Welcome to the Treehouse
02:00 The Dr. David Dao crisis, from the comms chief's chair
06:00 The fog of war, and why the first information is almost always wrong
10:54 Inside the Good Morning America apology
13:00 When your policies get in the way of your values
14:30 Miracle on the Hudson and the three flight attendants nobody named
18:36 The unsung heroes in Jim's own life
20:53 The 2am back pain that saved his life
25:00 Stage 4, and then the brain tumor
29:00 Losing his sight
33:30 "Cancer made me stronger. Blindness made my world brighter."
35:00 Writing Tailwind blind, on short-term disability
38:49 Ambition without purpose is a sailboat without a compass
41:00 Why me? Oscar Munoz and the two kinds of patients
44:49 Faith, gratitude, and a letter to God
47:37 Praying for what's already being made

Kelli Arena, CEO, Nat'l Cryptologic Foundation: How I Went From CNN to CEO

Season 1 · Episode 24

Monday, June 29, 2026 • Duration 57:15

Kelli Arena spent her career at CNN telling the public what powerful people would rather keep quiet. She covered the Justice Department, won an Emmy, and reported the Moussaoui trial, the only 9/11 case tried in an American civilian courtroom.

After Kelli left journalism, she went into another form of public service, serving as Chief of Communications for the National Security Agency, spending eight years helping the Agency find its voice.

Kelli has remade herself across four worlds: journalism, academia, government, and now the nonprofit sector, where she just became President and CEO of the National Cryptologic Foundation.

A few things she gets into, worth your time even if you never press play:

She took six months of maternity leave, three separate times, as an on-air correspondent. Everyone said it would end her career. It didn't. Younger women in the newsroom started thanking her, because she'd quietly given them permission.

She earned back America's trust at the NSA the boring way: Through Consistency. Relationships. A rule that every reporter got a callback within 30 minutes, even when the answer was "no comment."

And her advice for anyone starting over: "Listen more than you speak. Every single time I have listened to others before making a decision, it has been a better decision."

0:00:00 The Stumble that nearly ended my career

0:01:33 Meet Kelli Arena

0:02:52 A new chapter: President and CEO of the National Cryptologic Foundation

0:03:25 What cryptology is, and 500,000 open cyber jobs

0:05:30 AI's impact “can't be overstated”

0:07:30 Who gets displaced, and how we reskill them

0:08:40 Getting cyber smart as citizens

0:10:05 Becoming CNN's justice correspondent, then 9/11

Shalene Gupta, Editor, Fast Company: The Manager's AI Survival Guide

Season 1 · Episode 23

Friday, May 29, 2026 • Duration 18:02

Shalene Gupta, staff editor for Fast Company's Work Life and Leadership section, interviewed 35 middle managers at some of the biggest companies in the world for her piece "The Middle Manager's AI Survival Guide." What she found is that the contradictory headlines about AI at work aren't actually contradictory. There are two different worlds, and which one you're working in makes a world of difference.

One idea sits under all of it, and it matches what I find in my own work. People will walk through almost any change, AI included, when they trust that their leader has their back.

In this episode:

0:00:00 The question every manager is asking

0:01:20 The one-line takeaway from the AI Survival Guide

0:02:30 Two universes: the AI race vs. where most of us work

0:04:53 Ethan at Meta: "If you think they'll replace you, they probably will"

0:06:07 The math: a person vs. $200 to $500 a month in tokens

0:07:36 ClickUp's "100x more productive" memo

0:08:40 Are we weighing the human cost? (Dimon at Davos)

0:09:49 What it feels like to be a middle manager today

0:11:48 What the excited managers had in common (and a Georgia-Pacific surprise)

0:14:10 Advice for leaders taking teams through AI

0:16:26 Advice for the rest of us

0:17:07 My takeaway, and a look at next week

Links:

"The Middle Manager's AI Survival Guide" (Fast Company): https://www.fastcompany.com/91531056/the-middle-managers-ai-survival-guide

The Power of Trust, by Sandra Sucher and Shalene Gupta:

Dana Perino, White House Press Sec. & Bestselling Author: "Purple State" & Crossing Party Lines

Season 1 · Episode 22

Wednesday, May 6, 2026 • Duration 25:53

Dana Perino's new book is called Purple State. It's a political romance novel set in a gerrymandered Wisconsin district, about three young women who discover that love and friendship don't stop at party lines.

Coming from the 26th White House Press Secretary and co-host of The Five on Fox News (the most-watched show on cable news!), it's a book worth paying attention to. Especially as we find ourselves more divided than any time in recent history.

Dana talks about the personal story behind the book: The time a dear friend said, "Do not pass up the chance to be loved." She almost didn't listen.

Dana tells the story of sitting in the Oval Office with President Bush just before walking out to face a press corps hungry over a tell-all memoir from her predecessor. She was furious on his behalf. He told her something about forgiveness that changed her.

Purple State is out now. Pick it up today here:* https://amzn.to/4tRzGcZ

CHAPTER MARKERS

0:00:00 Welcome to the Treehouse Studio

0:01:13 The 2007 Phone Call

0:02:35 Life After the White House

0:04:58 Purple State: The Book

0:06:59 Why I Wrote a Novel

0:10:42 Wearing Your Politics Lightly

0:12:57 The Oval Office and the Forgiveness Lesson

0:15:52 68% of Young People Won't Date Across Party Lines

0:17:29 Do Not Pass Up the Chance to Be Loved

0:19:00 Peter, the Proposal, and the Open-Ended Ticket

0:20:05 Dinner With the Queen's Staff

0:21:46 There Is Freedom in Being Disciplined

Sue Gordon, Deputy Director of US Intelligence: What America Needs From Its Leaders

Season 1 · Episode 20

Wednesday, April 22, 2026 • Duration 01:36:54

Sue Gordon once oversaw 100,000 women and men of the U.S. intelligence community as Deputy Director of National Intelligence, the number two role in American spycraft.

She briefed Presidents Reagan, HW Bush, Clinton, W Bush, Obama, and Trump. She managed a $100 billion budget.

And in August 2019, she handed Vice President Pence her resignation letter with a handwritten note: "I offer this letter as an act of respect and patriotism, not preference. You should have your team. Godspeed, Sue."

Since then, life has come at her hard. Both parents died. Her husband Jim, the love of her life for 43 years, died unexpectedly. She has faced two rounds with cancer, the second one far more deadly than the first.

And she says she's the most blessed woman in the world.

In this conversation, Sue goes deep on:

The U.S. strikes on Iran and what she sees that most Americans don't
What the Epstein files actually reveal about how power protects itself
Why she almost ran for President
Why she quit the CIA with two weeks' notice to be a better mom
How the Trump administration publicly excoriated a 40-year career civil servant, and what she chose to do instead of fighting back
Why she thinks America needs to fix a system the Founders never designed for this much speed
What she wants every woman in a man's world to know, and what she wants the good men to finally do about it
The doorways of grief, and how to move through them

This is Sue Gordon in full: the spy, the mom, the widow, the patient, the patriot. Unfiltered. Funny. Occasionally heartbreaking. Always worth your time.

Find her podcast, Understandable Insights here:
https://podcasts.apple.com/us/podcast/understandable-insights-information-to-intelligence/id1827249845Books and Works Mentioned:

Outtakes: The President's Advice I Didn't Want

Season 1 · Episode 19

Wednesday, April 22, 2026 • Duration 04:02

A few times during my two-part interview with Judge and Rebecca Gonzales, they turned the tables on me. They listened. And they drew three stories out of me that I've rarely shared.

The first is a story that never made it into the main episodes: the Oval Office advice I didn't want that... changed my life.

The second is about what happens when your Quaker mother and your Jewish father sit down together at Hanukkah.

The third is about what shaped my decision to work for Attorney General Gonzales as a political appointee.

If you haven't heard Parts One and Two yet, start there. This bonus episode will mean more after you've heard their full story.

Content warning: Like part 1, this episode touches on childhood trauma and may not be suitable for all listeners.

If you'd like to support the show, please follow Stumbling Blocks on your favorite podcast app and leave a review. It's the best way to help other leaders like you.

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Stumbling Blocks: How Great Leaders Are Made – Details, episodes & analysis

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